DE3503485A1 - Verfahren zur herstellung reiner dialkylsuccinate - Google Patents
Verfahren zur herstellung reiner dialkylsuccinateInfo
- Publication number
- DE3503485A1 DE3503485A1 DE19853503485 DE3503485A DE3503485A1 DE 3503485 A1 DE3503485 A1 DE 3503485A1 DE 19853503485 DE19853503485 DE 19853503485 DE 3503485 A DE3503485 A DE 3503485A DE 3503485 A1 DE3503485 A1 DE 3503485A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation
- dialkyl
- carried out
- bar
- pressure
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 10
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 8
- 238000002844 melting Methods 0.000 claims abstract description 8
- 230000008018 melting Effects 0.000 claims abstract description 8
- 239000001530 fumaric acid Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000007858 starting material Substances 0.000 claims abstract description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 150000003890 succinate salts Chemical class 0.000 claims abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 150000002689 maleic acids Chemical class 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical class 0.000 abstract description 3
- 238000004220 aggregation Methods 0.000 abstract 1
- 230000002776 aggregation Effects 0.000 abstract 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 11
- 150000003900 succinic acid esters Chemical class 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- -1 alkyl fumarate Chemical compound 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- WWQSMJYMCWMODI-UHFFFAOYSA-N dicyclohexyl butanedioate Chemical compound C1CCCCC1OC(=O)CCC(=O)OC1CCCCC1 WWQSMJYMCWMODI-UHFFFAOYSA-N 0.000 description 2
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LZKIQTFJTSPBDX-YPKPFQOOSA-N (z)-2,3-dicyclohexylbut-2-enedioic acid Chemical compound C1CCCCC1/C(C(O)=O)=C(C(=O)O)\C1CCCCC1 LZKIQTFJTSPBDX-YPKPFQOOSA-N 0.000 description 1
- JDRMYOQETPMYQX-UHFFFAOYSA-M 4-methoxy-4-oxobutanoate Chemical compound COC(=O)CCC([O-])=O JDRMYOQETPMYQX-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WMNULTDOANGXRT-UHFFFAOYSA-N bis(2-ethylhexyl) butanedioate Chemical compound CCCCC(CC)COC(=O)CCC(=O)OCC(CC)CCCC WMNULTDOANGXRT-UHFFFAOYSA-N 0.000 description 1
- QCOAPBRVQHMEPF-UHFFFAOYSA-N bis(2-methylpropyl) butanedioate Chemical compound CC(C)COC(=O)CCC(=O)OCC(C)C QCOAPBRVQHMEPF-UHFFFAOYSA-N 0.000 description 1
- JDRMYOQETPMYQX-UHFFFAOYSA-N butanedioic acid monomethyl ester Natural products COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- BLKQQTCUGZJWLN-VAWYXSNFSA-N dicyclohexyl (e)-but-2-enedioate Chemical compound C1CCCCC1OC(=O)/C=C/C(=O)OC1CCCCC1 BLKQQTCUGZJWLN-VAWYXSNFSA-N 0.000 description 1
- HEJZJSIRBLOWPD-VHXPQNKSSA-N didodecyl (z)-but-2-enedioate Chemical compound CCCCCCCCCCCCOC(=O)\C=C/C(=O)OCCCCCCCCCCCC HEJZJSIRBLOWPD-VHXPQNKSSA-N 0.000 description 1
- JBJMZCVEBLDYCA-UHFFFAOYSA-N didodecyl butanedioate Chemical compound CCCCCCCCCCCCOC(=O)CCC(=O)OCCCCCCCCCCCC JBJMZCVEBLDYCA-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/40—Succinic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853503485 DE3503485A1 (de) | 1985-02-01 | 1985-02-01 | Verfahren zur herstellung reiner dialkylsuccinate |
| DE8585115159T DE3580165D1 (de) | 1985-02-01 | 1985-11-29 | Verfahren zur herstellung reiner dialkylsuccinate. |
| EP85115159A EP0190424B1 (de) | 1985-02-01 | 1985-11-29 | Verfahren zur Herstellung reiner Dialkylsuccinate |
| AT85115159T ATE57523T1 (de) | 1985-02-01 | 1985-11-29 | Verfahren zur herstellung reiner dialkylsuccinate. |
| HU86452A HU196945B (en) | 1985-02-01 | 1986-01-31 | Process for production of clean dialkyl-succinates |
| CS86708A CS271336B2 (en) | 1985-02-01 | 1986-01-31 | Method of pure dialkylsuccinates production |
| JP61018269A JPS61180742A (ja) | 1985-02-01 | 1986-01-31 | 純粋なコハク酸ジアルキルを製造する方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853503485 DE3503485A1 (de) | 1985-02-01 | 1985-02-01 | Verfahren zur herstellung reiner dialkylsuccinate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3503485A1 true DE3503485A1 (de) | 1986-08-07 |
Family
ID=6261436
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853503485 Withdrawn DE3503485A1 (de) | 1985-02-01 | 1985-02-01 | Verfahren zur herstellung reiner dialkylsuccinate |
| DE8585115159T Expired - Lifetime DE3580165D1 (de) | 1985-02-01 | 1985-11-29 | Verfahren zur herstellung reiner dialkylsuccinate. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585115159T Expired - Lifetime DE3580165D1 (de) | 1985-02-01 | 1985-11-29 | Verfahren zur herstellung reiner dialkylsuccinate. |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0190424B1 (cs) |
| JP (1) | JPS61180742A (cs) |
| AT (1) | ATE57523T1 (cs) |
| CS (1) | CS271336B2 (cs) |
| DE (2) | DE3503485A1 (cs) |
| HU (1) | HU196945B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5872276A (en) * | 1996-11-25 | 1999-02-16 | Bayer Aktiengesellschaft | Process for preparing dialkyl succinates |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19506096A1 (de) * | 1995-02-22 | 1996-08-29 | Bayer Ag | Verfahren zur Herstellung von Bernsteinsäure-dialkylestern |
| BE1011698A6 (fr) * | 1998-01-08 | 1999-12-07 | Pantochim Sa | Procede de production de tetrahydrofuranne, de gamma-butyrolactone et de butanediol. |
| WO2011017543A1 (en) * | 2009-08-07 | 2011-02-10 | Invista Technologies S.A. R.L. | Hydrogenation and esterification to form diesters |
| CN102070448B (zh) * | 2011-02-22 | 2013-04-03 | 湖南长岭石化科技开发有限公司 | 一种制备丁二酸二甲酯的方法 |
| CN113200853A (zh) * | 2021-05-19 | 2021-08-03 | 宁波窦氏化学科技有限公司 | 一种制备丁二酸二醇酯的工艺方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527345A (en) * | 1948-09-18 | 1950-10-24 | Allied Chem & Dye Corp | Preparation of esters of dichlorosuccinic acid |
| US4117242A (en) * | 1976-07-26 | 1978-09-26 | Phillips Petroleum Company | Suppression of side reactions in catalytic hydrogenation of diesters |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3830830A (en) * | 1972-02-29 | 1974-08-20 | Eastman Kodak Co | Production of dialkyl esters of succinic acid |
| DE2837022A1 (de) * | 1978-08-24 | 1980-03-06 | Hoechst Ag | Verfahren zur hydrierung organischer verbindungen |
| JPH0655684B2 (ja) * | 1984-11-21 | 1994-07-27 | デイビ− マツキ− （ロンドン） リミテツド | ブタン−１，４−ジオ−ルの生成方法 |
-
1985
- 1985-02-01 DE DE19853503485 patent/DE3503485A1/de not_active Withdrawn
- 1985-11-29 AT AT85115159T patent/ATE57523T1/de not_active IP Right Cessation
- 1985-11-29 DE DE8585115159T patent/DE3580165D1/de not_active Expired - Lifetime
- 1985-11-29 EP EP85115159A patent/EP0190424B1/de not_active Expired - Lifetime
-
1986
- 1986-01-31 JP JP61018269A patent/JPS61180742A/ja active Pending
- 1986-01-31 HU HU86452A patent/HU196945B/hu not_active IP Right Cessation
- 1986-01-31 CS CS86708A patent/CS271336B2/cs not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527345A (en) * | 1948-09-18 | 1950-10-24 | Allied Chem & Dye Corp | Preparation of esters of dichlorosuccinic acid |
| US4117242A (en) * | 1976-07-26 | 1978-09-26 | Phillips Petroleum Company | Suppression of side reactions in catalytic hydrogenation of diesters |
Non-Patent Citations (2)
| Title |
|---|
| US-Z: Chemical Abstracts, Vol.100,1984 Ref.23918c * |
| US-Z: Chemical Abstracts, Vol.98, 1983 Ref.34252x * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5872276A (en) * | 1996-11-25 | 1999-02-16 | Bayer Aktiengesellschaft | Process for preparing dialkyl succinates |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE57523T1 (de) | 1990-11-15 |
| EP0190424A2 (de) | 1986-08-13 |
| EP0190424A3 (en) | 1987-07-29 |
| CS70886A2 (en) | 1989-10-13 |
| JPS61180742A (ja) | 1986-08-13 |
| HUT43996A (en) | 1988-01-28 |
| CS271336B2 (en) | 1990-09-12 |
| DE3580165D1 (de) | 1990-11-22 |
| HU196945B (en) | 1989-02-28 |
| EP0190424B1 (de) | 1990-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OM8 | Search report available as to paragraph 43 lit. 1 sentence 1 patent law | ||
| 8127 | New person/name/address of the applicant |
Owner name: CHEMIE LINZ (DEUTSCHLAND) GMBH, 6200 WIESBADEN, DE |
|
| 8141 | Disposal/no request for examination |